


Mongoose and Jailbird

by Moonstone_Plus



Category: Bunk'd, Walk the Prank (TV)
Genre: Anal Sex, Beach Sex, Bisexual, F/M, Gay Sex, M/M, Oral Sex, Rough Sex, Semi-Public Sex, Smut, Threesome - F/M/M, Underage Sex, Vaginal Sex
Language: English
Status: In-Progress
Published: 2020-09-05
Updated: 2020-09-05
Packaged: 2021-03-06 19:54:34
Rating: Explicit
Warnings: Underage
Chapters: 3
Words: 13,539
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/26294467
Author URL: https://archiveofourown.org/users/Moonstone_Plus/pseuds/Moonstone_Plus
Summary: Herman Baldwin heads off to cliff dive meets up with Griff Jones who decides to join, and a quick friendship forms.
Relationships: Griff Jones-McCormick/Bailey Schuster, Herman Baldwin/Bailey Schuster, Herman Baldwin/Griff Jones-McCormick
Kudos: 2





	1. Chapter 1

“Your butt is showing,” 

Herman Baldwin’s ears pricked and he looked back at who was talking to him. Kneeling on his hands and knees, sinking a little ways into the soft sand, he hadn’t noticed his trucks slipping down his ass to show off some skin. Just a sliver of his ass, revealing his little crack to anyone who looked over. Luckily Blake, his older cousin, pulled them up with a smirk. An annoying, superior smirk.

“Trying to attract guys?” Blake snickered.

Rolling his eyes, Herman growled out a response. He wasn’t entirely sure why his cousin seemed to think that he was interested in dudes all of the time. “I have a girlfriend, remember…”

Tugging his cousin’s trucks a little roughly, Blake got in a peek of the boy’s round, smooth butt. Nothing much, and nowhere near enough to be noticed as being dirty. He loved seeing that perfect little ass on display all the time, but wanted a boy to take care of Herman first to see how he liked it. “Bailey? As if,”

“I am dating her!” Herman whined. “You even saw us off on our first date!”

“Who takes a girl to the arcade, dude? You’ve taken me better places just to hang out,” Chuckling to himself, Blake gave the boy’s butt a small kick. Herman slipped forward into the sand, then rolled over to glare. “Aww don’t be sad Hermie.”

“S-She had fun!” Herman pouted. “I even got a kiss!”

Coming over with a towel wrapped around his waist, Chance snorted. His wet feet were coated in dark sand, having just come back from a little swim in the ocean while his brother was trying to build a sandcastle to no avail. With a cocky tone, he loomed over Herman’s helpless self sitting in the sand. “Barely bro, I’ve gotten better kisses from Bailey… and at least mine weren’t on the cheek.”

Herman sneered at the older boys standing over him. 

“Bailey did not kiss you, Chance! A-and mine was on the lips,” He shouted defensively, “We made out outside the door when I dropped her off at home.”

Chance simply chuckled, deciding to tease his little brother. “Oh come on, you know she has properly kissed me… What do you think of the fact that I’ve gotten further with your little girlfriend…”

Even Blake snorted at Chance for that comment. The older boy nudged him, picturing Herman making out with the adorable young girl he hooked up with after so long. Something in that image made Blake twitch. However, in his loose trunks the sixteen-year-old’s cock went unnoticed by the other Baldwin boys. “If you weren’t his brother, you could just show him the kiss you gave her,”

“Could always just give you the kiss…” Chance teased back, eyes roaming up and down his attractive cousin’s body.

Herman and Blake gave him a look before replying in unison: “Ew!”

Chance rolled his eyes. “Oh come on, it’s not like I’m kissing Herman, that would be ew.”

After picking himself up from the sand and moving a few steps away from the strange older boys, the youngest Baldwin packed away a few of his things, then grabbed a couple chocolates to stuff into his pocket. If only he had noticed then that they were warm and squishy, about to hit their melting point as the hot summer sun roasted them through his small bag. Herman straightened up, turning around to find the pair arguing over who would kiss who and how one or the other was being gross about the whole thing. In his mind, they were both being gross. Talking about kissing Bailey was bad enough, but Herman couldn’t see himself kissing Blake, let alone Chance. Even seeing them shirtless occasionally made him want to gag. The boy struggled to see them as anything past his brother and his cousin.

“Oi losers!” Announcing himself to them over his shoulder, turning on one heel, Herman started towards a tall cliff in the distance.

When coming here for vacation somebody on the plane had spoken about how fun it was to climb up the cliff side, rock climbing without need for tools. Apparently the water below was quite deep and free of any rocks. The moment that was said, Herman knew he just had to find it and go diving at least once. This was his chance to leave mostly unnoticed, as the older boys fighting could go on for hours and swap from one thing to the next just by saying one word.

His little feet sunk into the sand with each step; Sunlight roasting Herman’s back and ass, which had slipped down again for Blake and Chance to lick their lips over.

“While you two fight like an old married couple, I’m going to go diving. And NO following me.” He smirked, knowing that they would easily try to come along so the annoyance could continue.

He travelled for a while, until he finally found a good spot to dive from. With the stone beneath his fingers was cool and smooth to the touch, almost like it would slip out from his grasp. Not to say that had not already happened; Some loose pebbles are not the strongest handhold. It wasn’t too far a fall, but still a feeling of dread ran through a fourteen-year-old boy clinging to the rocky wall for dear life. Heights was a bad idea that he refused to mention to anyone else. Digging his slender fingers deeper into one of the small grooves that formed a hand-hold, the young boy steadied himself until raising one leg to find the next place in the stone wall. With some difficulty, he kept climbing slowly upwards. His muscles hurt like hell, and with each movement it only got worse for him.

“Why did I decide to do this, there was a stinkin’ path!” The boy grumbled to himself, as he looked up at the rock wall that stood in his way while running a hand through his slightly curly black hair.

Daring to turn his head just slightly, Herman Baldwin looked out across the sparkling almost crystal blue ocean and further hated his choice. The golden beach, clear water and even little crabs that made their hole in the shore all looked so much more beautiful and alluring than some stupid rocks.

With a loud sigh, Herman reached out and took the next rock.

Of all the things that were happening on the Isle currently, the teen had decided on relaxing away from it by doing some cliff diving despite protests from his older brother and cousin, who had completely refused to come with him. Not wanting to miss any of the fun that would be happening on the beach. Thus, it left the fourteen-year-old boy to make his way towards the cliffs and up to the optimal jumping height.

He wanted to dive, not flatten himself.

“Just a little further,” He groaned, climbing ever higher. The boy struggled not to look down since he knew he would freak and lose his footing and nerve if he saw just how far he was up.

After a solid five minutes of climbing, Herman was finally pulling himself up onto the cliffside and onto the tick grass. Red in the face and out of air he collapsed into the softness and spread out his body-wide. With a heaving chest, the boy stared at the sun from behind closed eyes. The teen rested a few moments, before sitting up and almost whining.

“You have to be fucking kidding me!” Herman swore, noticing that the cliffs that he could dive off safely were still a short walk away. Something that had, the already breathless teen groaning.

Stomping along the path felt like it was taking forever, and taking in the sights from down below was like torture. Kids ran around screaming as the sand burned their feet before cooling off in the water - Herman wanted so badly to cool off down there - while their older brothers and sisters, or their parents could relax down on towels eating ice cream or drinking soda. Something, in particular, caught Herman’s eye, however: A young couple hidden away in a shallow crescent-shaped cavern with little to no clothes on. One was a fairly attractive brown-haired girl, and she was up against a wall with both legs wrapped around some older looking boy’s waist. They were so close that they would have to be making out. And by the way his hips were going at it, the girl’s pussy was getting the fuck of a lifetime.

Herman watched for a solid few minutes, with the aching in his pants unbelievable. Gulping, the boy wished he had gone there rather than up a lonely cliff.

A wish that only grew when he heard a name being moaned by the girl. “J-Jo-JONAH!”

‘Damn, that girl is lucky. Jonah has such a cute ass… and now has the sexiest name in the world. Great!’ Herman thought with a very long groan. There was Jonah at his school, some popular kid he had never met. Looking back over the edge, that boy was gone from his mind. 

After kicking a rock the path was back to being followed, but it was now significantly shorter. Especially when Herman bothered to notice the little things sitting there almost hidden by the tall grass.

“Um… hello?” He called out.

Crickets and the moans stemming from the young couple were the only noises that responded to him. The teen looked a little confused before beginning to move towards the cliffs once more.

Quietly through the blades of grass and over to the thing sitting on the edge with both legs swaying over the edge. Herman cocked an eyebrow and tapped their shoulder. A boy’s cute face turned to greet him, wearing a look of panic. 

“Don’t push me off!” They yelped, with the frightened boy clinging to Herman’s shirt for dear life. After a moment he let go and blushed. “Uh, sorry. Bad experience with cliffs when I was younger.”

“What the heck happened?” Herman couldn’t stop himself from asking, as the boy fixed himself up.

“My girl at the time’s brother decided to prove he was responsible by taking us on a hike, and my girl and I fell down the cliff.” The boy the dark-browned haired boy shivered. Even Herman shivered thinking about it. Something told him not to jump off the cliff now.

Extending a hand, the dark-haired prankster grinned. “I bought some chocolate with me, want some?”

“Uh sure, but why? Why did you bring chocolate to do whatever you're doing up here,”

Herman simply giggled at himself. “I’m an idiot who forgot it was in my pocket.”

He shrugged when all he got in response was a deadpanned look.

The two quickly retired to a small, smooth rock formation that was close by and away from the cliff, while also close enough that both boys could now hear the moans stemming from the young couple. It had been both funny to explain that noise and arousing when the two got a peak. Long and short of it all, two horny teenage boys were sitting on rocks and one was trying to fish chocolates out of his pocket.

When Herman’s hand came back out it was sticky, dripping with a sugary brown mess and caramelized. He raised his hand and shook it. 

“Ughhh, it melted!” 

The other boy gave it a slightly disgusted look. “How long has that been in your trunks?”

“It’s a hot day!” Herman snapped. After wiping the hand clean on some grass, he noticed just how squelchy the pocket felt. A shiver ran down the boy’s spine. “O-oh gosh, I am not wearing these !”

The boy gave him a look of sympathy. “Did you bring a towel? Or at least is your hotel not too far away?”

Herman shook his head. “No! B-but my boxers are underneath my trunks. They look normal,”

All Herman had on at that moment was a pair of black trunks with two white lines running down either leg. Underneath was a pair of camo-themed boxers that were a size too big, since they belonged to his cousin Blake. So if you ignored the cock almost begging to escape the slit, Herman would be in normal clothes going back.

“At least you choose boxers, boxer-briefs are way too noticeable to be used like that.”

“Yeah. Could be worse, could have worn some tighty whiteys,” Herman giggled.

“That would be hilarious, everyone would have looked.”

“Yeah, including you. Since you would be staring at my ass the whole way back,” Herman snickered playfully, loving the way the other boy just rolled his eyes. Yet made no attempt to not take a look. “Pretty sweet butt, huh? Uh… what’s your name?”

The boy answered with a smirk and a spank on Herman’s ass when said boy had turned to tease him with a peek at said ass. “Griff. But I think my butt’s better,”

“Griff? Like Griffin?” Herman questioned, after releasing a semi-embarrassing yelp. “Herman by the way.”

“If it was Griffin,” Griff groaned, a little annoyed at getting that question for what felt like the millionth time in his life. “I would say, Griffin.”

“Jeez… I was just asking.” Herman pouted while not getting anything from the other boy, but a look. Getting to his feet the fourteen-year-old started to untie his shorts, before looking towards the other boy. “You don’t mind, do ya? these are getting a little sticky.”

Griff shook his head while propping himself to one side, better able to watch lazily as this random boy began to strip near-naked in front of him. A soft moan left the teenager’s lips as Herman started, ignoring the stare. That younger boy’s ass was so soft and round looking that it was easily making Griff twitch; with neither noticing that this was a bigger turn on for them than Jonah’s girl screaming out in pleasure. Though both of the boys would be lying if they said they weren’t a little turned on from the girls moaning. For just a moment Herman’s trunks caught and tugged his boxers too. This gave Griff a peek at his pale ass, before being covered up in a movement that was much too slow to not be deliberate.

“Damn dude, for such a tan, your ass is pale as f’ man” Griff stated, knowing that the ‘peak’ wasn’t accidental.

“Saw that did you?” Herman smirked without looking back. He tugged off his ruined trunks and kicked them. “It’s not that pale!”

“I’ve seen brand-spankin' new paper that was less white than that thing.” Griff teased.

“Okay then let’s see how pale yours is!” Retorted Herman, crossing his arms. When he turned around, the sandy-haired brunette could see a hint of his pale dick through the slit. Griff gulped, being mistaken. “Oh, too scared?”

“Nah, I just don’t show my ass to random boys I met on a cliff.” Griff teased.

Putting on a sly smirk, Herman teased his ass once more. He held the hem down, showing the start of his crack. “Well, you’re Griff. And I’m Herman. So it's not just random now?”

“Doesn’t mean I'm jumping to show off my butt.” Griff chuckled, as he patted the spot next to him. Subtly motioning for the other boy to join him once more.

Smirking broadly as Herman took the seat next to him, the juvie boy turned onto his back and looked up into the sky. Clouds were few and far between, showing off a clear blue sky that stretched on forever. But, from the corner of his vision, all that had Griff’s eyes was Herman’s stiff cock jutting up and bulging inside of his cute camo boxers. Noticeably too big for the younger boy, Griff began to consider swapping underwear, or at least giving Herman his trunks and swapping into those boxers. All Griff had underneath were some tight blue boxer briefs.

Putting both arms behind his head, Herman whistled to himself. Wondering silently about how he would ever explain the chocolate, the boy decided in the end that he could probably just kick them off the cliff and get some new ones. Herman turned slightly to one side and saw Griff’s eye jerk away. Both boys were fully aware of what the other one’s thoughts, which only fuelled their egos and pumped more blood into their young cocks. 

“So, what are you going to do?” Griff questioned, to break the silence building between them.

“I don’t know. But I can’t wear these! My dick is hanging out,” A slip of the tongue later would have revealed Herman knew Griff saw.

Griff shook his head in amusement. “Well, that’s going to be a fun walk back to your hotel isn’t it.”

“I mean,” Grinning broadly, Herman jabbed a finger at Griff. “You could let me ride on your back so nobody can see?”

“And have a cock poking me?” Griff snorted, clutching his sides and beginning to laugh. Though this was all a show; the juvie turned rich boy wanted to feel more than just that cock poking him. “I might not feel that small thing but still ew, no thank you, Herman! I would rather go back to Juvie,”

“Oh come on! We are both dudes! Being in Juvie, wouldn’t you be used to having cock’s poking you?” Herman teased a little.

Griff deadpanned at the joke, then nudged the other boy. Expecting Herman’s stomach to be soft, surprisingly the boy was firm. “Har, har dork! Why don’t we just swap clothes? So much easier,”

Herman was a little confused about how his cock reacted to that offer.

“We, um, could...” Herman blushed, nervously.

Griff started to untie his trunks, casting a friendly smile at the other boy. Much to Herman’s disappointment when he slipped them off, his underwear did not come with. Tugging his blue-and-pink trunks off of a foot, Griff was left in a tight pair of blue boxer briefs with Calvin Klein on the hem. Bulging heavily, much like himself, Herman gulped at the sexy view of his new friend. A view that was cut short by some shorts shoved in his face.

“You know if you are going to stare you could actually do something to earn it,” Griff commented, rolling his cute brown eyes.

Herman raised an eyebrow. “Like what? I ain't sucking your cock or anything dude.”

Snorting at the younger boy, the ex-thief ran a thumb around the hem, teasing it open just enough that Herman could see his thin treasure trail but not the cock itself. When the hem snapped back to his waist, Griff grinned at the awestruck look he was getting.

“Who said anything about sucking? Or even touching my dick?” He asked playfully, “That one you would REALLY have to earn!”

“Then what, dork?” Herman questioned, the boy not entirely knowing how to handle this situation since normally he would have Chance or Bailey around.

Griff chuckled and gave the boy a look. “Now, now, don’t be calling me a dork if you want my shorts.”

They fell into an awkward silence for a minute or so in which neither was willing to give up what the other painfully obviously wanted; with both boys just looking down and playing with rocks rather than their cocks. Words came to mind, that was no issue. Just a matter of who said what first.

A little crab, who had been left there by a little girl, scuttled into Herman’s pocket while they weren’t looking. 

Finally, with a rejuvenated smirk, Griff broke the silence once more. 

“Well before you started towards me and I well you know, I was about to find somewhere quiet to uh, jerk off. I uh- I could use some company?” He offered slyly. “If you want those shorts, of course.”

“You’re inviting me to…” Herman started, eyes widening slightly. Despite knowing what this Isle was known for, he hadn’t expected it to be this easy.

When he looked back over any other words died in his throat. 

The other boy had already pulled his cock out of his boxer briefs.

Griff’s cock was a beautiful five-inches, with a very slight curve and a rich whitish tan to match his body. Not the thickest cock by any means, but on Griff, it looked nice for its length. Fuzzy balls and a wild yet small bush, the cute rich boy’s cock was led by a thin treasure trail that barely reached his bellybutton. The head was a pale shade of pink and flowed nicely down to his shaft. Able to make Herman twitch just by looking at it, Griff couldn’t help but smirk.

“I see you like it,” Griff chuckled, with the ex-juvie boy’s hand cupping his cock and giving it a slight squeeze. “So are you going to earn my swim trunks dude? Which you will have to return later by the way, or shall I put this away?”

Herman wordlessly reached down and unbuttoned his camo boxers, fishing his cock out. 

While smaller at four and three-quarter inches, Herman easily had in some later opinions, the cuter of the two cocks. Completely shaved, his pale dick stood out against the tan of his body, just like the sliver of his bubbly butt Griff had seen. A much deeper pink took the head of Herman’s cock. And his balls were small, hanging loosely in the Summer heat. Wearing his boxers still made a surprisingly sexy sight, only seeing his cock out.

“Damn,” Griff gave his cock a stroke, smirking a little as he decided to tease his new ‘friend’. “Not bad Herman! So do you shave? Or can you just not grow any pubes down there?”

“My girl prefers not to gag when she goes down on me,” The other boy blatantly lied.

Griff rolled his eyes. “And does this ‘girl’ have a name or is she just in some nudie mags?”

“Bailey!” Herman retorted with a proud smirk while wrapping the hand around his cock. Stroking himself nice and slow, the boy with dark curls let a traitorous moan escape his thin lips.

“Cute name, for a made-up girl.” Griff teased while moving down into a sitting position next to the slightly younger boy. The fifteen-year-old’s hand matched the other boy's beginning strokes. “Since you’re too much of a dork to admit she isn’t ‘real’, have you and her ever done stuff?”

Kicking himself and lack of experience, the prankster shut his eyes and kept jerking. “Yes. Blowjobs.”

“That’s nothing!” Griff snorted loud and obnoxious, elbowing Herman in the sides. “My ex and I did everything! I even did her big sister.”

“That’s the biggest load of bull I ever heard!” Herman giggled, cracking an eye open to watch Griff moving along his cock. The hand moved slowly up and down, with the older boy even teasing the head with his thumb. Herman tried it himself and whimpered at how good it felt.

“Oh, well if you come back to my hotel room I can show you videos of that biggest load of bull,” Griff smirked, making Herman’s eyes widen very slightly as he wondered if Griff was telling the truth.

What Griff wouldn’t mention was that it was more than just girls in his videos, with the boy having played around with his older adopted brother a few times when they got bored and horny. Usually this was with a girl in the room leading to harmless teasing, but once or twice they had gone further and Xander had sucked his little brother’s dick. Something surprising about the hunk was that he was happy to bottom if it made the other person happy. He learned it early into camping life with a few counsellors and other campers, all of whom loved when power versatile Xander McCormick came to Kikiwaka.

While he tried getting Griff into all of that stuff, the younger boy rebuffed it saying he had enough bottoming in juvi to last him a lifetime. Xander could respect that and let the matter drop.

Herman couldn’t begin to imagine Griff fucking some girl. What did they look like, how old was she, did he get them both at once. All of it drove the boy to moan. “I-it’s a date. N-not a date, date! But a… Oh, you know what I mean! Y-you couldn’t date the Mongoose anyway,”

“Good, I don’t date animals.” Griff teased, before smirking. “The mongoose would be lucky to date me…”

They fell into a comfortable silence broken only by the sound of their occasional young moans and heavier breathing that drifted off into the air and were carried off with the wind. Herman’s hand moved along his cock slowly and teasingly, making a shiver run down his spine and the boy bucked up into the air. Everything for him tingled, not far off an orgasm. Meanwhile, lying beside him Griff took a faster approach. Furiously jerking his cock, grunting and moaning louder than Herman, the fifteen-year-old boy’s hand looked more like a blur. His hand slapped his balls every now and then, making an amusing ‘fapping’ noise.

Griff threw his head back, jerking off furiously in an attempt to cum first. He was good at that, cumming whenever he wanted to. It helped whenever he needed to shoot a quick load without getting caught. The amount of times it allowed him to cum in Xander’s jockstrap before the older boy came back from a shower was unbelievable. 

His other hand roamed his smooth chest, massaging gently and teasing his nipples. 

Herman paused and watched for a while. He could see the drop of precum dribbling out of Griff’s cock, which made the boy lick his lips.

Griff paid no mind to this, simply scooping up the drop and swallowing it in one gulp. Knowing full well Herman would be jealous he didn’t get any, the boy stuck his tongue out. Mumbling something close to ‘want a taste, dork?’, he was rebuffed by the other boy.

“You are gross!” Herman commented playfully while playing with his soft, smooth balls. 

Opening his eyes to the sight, Griff moaned softly. Reaching over, he slapped away Herman’s hand and cupped his balls. “They’re so smooth, what’s it feel like? Fuzzy ones tickle,”

He didn’t receive an answer with Herman instead moaning from the feeling of Griff’s hand around his balls, with the fifteen-year-old’s rougher hand from his time at camp and in juvie, giving an extra feel to it. Griff once again rolled his eyes due to the slightly younger boy and continued to fondle the smooth young balls, before moving upwards and taking over from Herman’s hand.

“O-Oh god!” Herman moaned, as Griff’s hand wrapped around his cock. With the younger boy loving the feeling of having the other boy’s hand wrapping around his sensitive erect cock. Quickly learning that Griff’s hand felt far better than his own hand.

“Fuck you’re twitching! Gonna shoot?” Griff teased, using his fast pace on Herman in hopes of making the brunette boy shoot his load, hard.

“N-No!” Herman protested. “I c-can last!”


	2. Chapter 2

Despite the young boy whimpering and attempted protesting, Griff didn’t believe a word of it. Instead, he got up onto his knees then slung one over Herman’s legs. Looming over the younger boy, he moved down and pressed their cocks together, gripping them both with one hand. He was so close and knew Herman was too, so started to jerk them off as one. Herman cried out in shock and pleasure, writhing around on the rock as Griff worked his cock.

Thrusting his hips, the fifteen-year-old fucked his palm and grinding against Herman’s cock. Zuri and Emma would have loved seeing that, or being in the hand’s place.

Herman gripped at the rock and bucked his hips as the pace became too much. Milked by Griff and the heat of his cock, he shouted out before beginning to cum all over his tanned chest. His cum flew high, with some managing to hit the sexy older boy. It splattered all over him, far enough to get some on his lips.

This didn’t stop Griff, however, who kept jerking off their cocks together. If anything, he only went faster. 

“O-OH SHIT! F-Fuck! I’m cumming too!” 

Turned on by how powerful Herman’s orgasm had been, the teenager grunted and let out a loud moan as he too shot a load all over Herman. His wasn’t as far but managed to hit the boy’s nipples at least. Some dribbled from his cock and onto Herman’s, then down around the boy’s balls. What was on his thumb was quickly licked up.

“Want a taste, Herman? I’ll consider letting you keep those trunks if you do,” Griff teased, despite not planning on letting him either way. Just wanted to make the slightly younger boy eat his cum.

Herman hesitantly licked his lips clean of his own cum, then looked down to see his body coated in thick, white teenage cum. He couldn’t work out what was his and what was Griff’s until a thumb was jutted at him. A thumb coated and dripping of teenage spunk, which he very nervously took into his mouth. Sucking and licking at it, Herman tasted the sweetness before swallowing it all. He kept on sucking for a while, before pulling off with a pop!

He nodded curtly. “Mongoose approves,”

“I’ll let the snakes know,” Griff smirked, not bothering with the eye roll this time.

“Something tells me your ‘snake’ knows,” Herman grabbed their cocks then lazily stroked them. While it wasn’t enough to make either of the boys moan, Griff looked over and gave Herman a grin as he continued to stroke.

“It may. Who knows, maybe I should go let it talk to your girlfriend, she could tell you.” Griff teased, wanting to see what the boy thought about possibly bringing their girlfriends into the fun they were enjoying. “I bet she would love to have a snake taking control instead of a little mongoose…”

“We both know that the Mongoose isn’t little!” Herman pouted, before giving the other boy a look that told the older boy to shut up. “She can’t have it until I get a turn.”

“Oh, so the mouths free… since apparently you got that?” Griff questioned, knowing he was pushing some buttons.

Herman groaned. “Dude, stop talking about my girl when we are lying on each other covered in cum!”

“So when I nut inside of you I can talk about her?” Griff smirked with a throbbing cock and a sly attitude. Still hard and leaking precum, the boy couldn’t help but want a piece of Herman’s cute bubbly ass. So he moaned a little, just below what the other boy could hear.

“You are-” 

Herman groaned, unwilling to admit that the boy was cute. Something that had been one of the biggest reasons for how willing he had been to just jack off with some strange boy. He opened his mouth to argue further but found Griff lowering down and running his tongue through a thick puddle of their cum. Moaning in surprise, Griff continued to lick up their cum. He could see it building upon the boy’s tongue and in his mouth, giving him a thick white throatful of spunk. 

Turned on by the sight of it, Herman shivered. Eventually, Griff’s tongue found his nipples and proceeded to trace around the small pink nub. 

Griff was in love with their taste and determined to get more. Working his tongue and hands all over the young cute boy with lightly defined abs, the fifteen-year-old licked up every drop he could find. Even the one on Herman’s lips. 

“You just licked me!” Herman’s eyes went wide in shock. 

Shrugging, Griff grinned at the other boy. “In for a penny, in for a-”

Without finishing his sentence, Griff’s lips were pressed against Herman’s, with the boy’s tongue invading his mouth still coated in their hot cum. Herman couldn’t resist the temptation to allow it in, and start forcing cum into his mouth. Tasting it from the other boy and his saliva, he moaned down Griff’s throat. So sweet and salty all at once, he wanted all of their load. However, Griff stole most of it and swallowed it with a very loud gulp. After which his mouth opened to show it was all gone.

“-pound.” He finished. “Now swallow before I steal your half.”

“There wasn’t another way of giving me some!” Herman blushed, shocked the boy he had only met a little while ago had kissed him.

Griff chuckled to himself and was tempted to do it again. “I wanted to kiss you? By the way, I’m actually in to pound you if you are,”

Herman nervously kept quiet for a few moments, listening to the breath of the boy above him and the occasional moans coming from the couple nearby before deciding to go for it. “In for a penny, r-right?”

“Awesome, dude!” Griff said eagerly, then in a surprise move offered the boy two fingers. “Suck on these for me,”

Herman whispered the rest of the saying to himself, before opening his mouth and allowing Griff’s fingers to enter. Griff grinned at the curly black-haired boy as he sucked away on his fingers, using his tongue to tease each before letting them slip out with a pop. The cute pink tongue lapped at his digits for good measure before Griff climbed off and Herman obediently rolled over. 

Shifting lower on the rocks and sinking his knees into some sand, Herman’s perfect ass was put on full display. 

A sight that only got better as Griff tugged down the back of those too big camo boxers and finally saw the ass he had wanted for the last half hour. He grinned at how cute of ass the slightly younger boy had, even his ex’s and her sister’s ass hasn’t been this cute. Moaning internally, he ran a hand around the soft cheeks. Just like a cloud, and even paler. Griff used his thumb to spread Herman’s cheeks apart and get a look at the boy’s hole. 

“So fucking hot!” He grinned, loving the smooth pink rosebud. “So fingering alright?”

Herman nodded, not really experienced with taking things in his ass but knowing enough from a few videos that Bailey had made him watched, that had included a couple of boys with a girl. While he attempted to focus on the big breasted women, his eyes drifted. Something that had made him feel a little self-conscious as Bailey almost drooled over the massive cocks, even if she did keep saying how good his cock felt was when they groped each other while making out. Pressing his index finger up against Herman’s hole, the older boy running a hand down Herman’s spine forcing the fourteen-year-old to shiver a little from the touch.

“O-Oh god…” Herman whispered as Griff’s hand continued to rub his back. 

As his hand moved towards Herman’s cute bubble ass, Griff questioned the boy. “You okay, dude?”

“Mmmm…” Herman nodded.

Griff grinned and cupped the boy’s ass cheeks and gave them a firm squeeze, earning yet another moan from the teen below him. Something that had his cock throbbing. While he wanted to slide deep into the bubble ass right then, he knew from first-hand experience that doing it would hurt badly. Thus he ran the tip of his finger against the hole of the boy, who moaned as the finger pressed finally against the entrance.

“I’m going to push in now dude,” Griff stated, causing Herman to stiffen a little before relaxing when Griff rubbed his back in order to soothe him. 

Very slowly and carefully, his somewhat lengthy finger slowly eased into the bubble bum of the fourteen-year-old. The teenager below him squirmed around the finger until Griff’s entire finger was completely inside of him and the thin finger had begun moving inside of him. Griff continued this for a few minutes until Herman was no longer reacting negatively towards the sensation, which is when he pulled out enough to push in with a second finger, earning a loud moan from the slightly younger boy.

“Oh god, G-Griff!”

Griff couldn’t help but giggle as he decided to tease the bubble butt cutie. “Wait until it’s not my fingers before you call me that.”

Groaning as he put his head against the stone, Herman grit his teeth feeling his hole begin to stretch open for those digits. The tips widened him before Griff fully pushed deep inside with one powerful shove. While Herman winced, he took the pain and let out a moan. 

“F-Fuck…”

Griff’s slender fingers brushed against his prostate, causing the boy to cry out a sound of euphoria. “Holy shit! Fu-fuck me…!”

“N-Now?” Griff questioned. While it was leading up to it, he didn’t think Herman would let him fucking him this fast into the fingering.

Nodding very slowly, the dark-haired boy’s moans quieted despite how good he felt. 

Bullets of sweat ran down his forehead, with the sun cooking both teenage boys and tanning up their mostly naked bodies. Griff’s cock, cupped by his boxer briefs that still covered his ass, quickly lined up with Herman’s sweet virgin hole and tested the waters. By pressing against it and seeing how loud Herman moaned, Griff waited for the boy to loosen up a little more. Running his hands up and down the boy’s smooth sides and teasing Herman’s sweet little nipples helped to soothe him, and the wincing became needy little moans. 

“I’m going to put my dick in now, dude. Are you sure you can take it?” He questioned in spite of how badly he wanted to ram it in there and get to fucking.

Blushing, Herman replied. “I-If your ex could, I can take it! Y-You’re not that big!”

Griff pouted at that comment. 

“I’m bigger than you!”

“So let me feel iiiit- Aaaaah!” Herman’s mouth fell open like a gate as the head finally pushed inside of his virgin ring. Somehow it felt bigger than before. “Ow, ow, ow! O-okay it’s big!”

“Mmm, your ass feels way better than my ex’s pus, dude!” Griff beamed, moaning from the feeling of Herman’s virgin ass squeezing his cock.

Slowly pushing deeper inside, the boy’s cock was hugged tightly as it reshaped Herman’s innards. An overwhelming heat filled them both that grew hotter and more passionate with every inch of Griff that moved deeper into Herman. Griff continued to feel up the sexy younger boy now that three inches of his cock were inside. He stopped and pulled out to the head, then back in with a deeper thrust. 

Throwing his head back, Griff silently moaned. His cock was being gripped so tightly it felt like Herman was about to tear it off. “Ho-holy… oh damn, Herman! You are soooo tight!”

Herman blushed a little, wondering if being tight was a good thing but the teen was unable to ask the question as all that was managing to escape from his mouth were moans of pleasure as his ass was stretched open by the lengthy dick of the boy he met now a couple of hours ago.

Griff fucked the virgin ass gently, denying the young boy his whole cock. Just enjoying how tight the little bum was as he used it, the boy grunted and kept thrusting in and out. Soon Griff spat on his hand, before grabbing his throbbing cock to get it slick. When he put it back inside, he forced his cock balls deep.

“Ngh! S-sooooo good!” 

Herman gasped, feeling it as his new friend’s cock throbbed inside of him. His cock was twitching and dripping with pre. Using deep, faster thrusts that put both of them on edge, Griff’s hips snapped back and forth to fuck the boy harder. Slamming against Herman’s prostate became easy with some practice and soon he was hitting it every time. 

“Oh god, G-GRIFF!” Herman found himself screaming, the boy blushing as his scream reminded him of the one he heard from the girl as he walked towards where he was now being fucked.

“You feel amazing, dude!” Griff grinned.

As his thrusting inside of Herman continued, Griff watched as the younger boy lost the ability to form words between his moans, with Herman becoming a mess of noises and heavy breathing. The teen pushed himself backwards with each of Griff’s thrusts, in order to take the five-inch cock deeper inside of him before releasing a loud moan as his pale bubble butt was stretched and pounded open. With the profuse amount of sweat pouring down their tanned bodies, Herman’s hands slipped on the smooth rock. The thrusts from behind started to get harder, making him gasp and slip a little. 

“Let's swap positions, Griff…” He breathed, “I want to ride you,”

Griff grinned as he recalled the numerous times of having the large breasted Emma Ross bouncing on his cock, with his hands behind his head enjoying the view of her breasts bouncing. He blushed a little when Herman released a loud moan from the throbbing of his cock inside of him, before easing out and moving around so he was lying on the rock, not realising until he did it that he had laid in a good-sized puddle of Herman’s pre-cum.

After hooking his hands under the boy’s arms and using a lot of effort, Griff managed to pick the boy up. This caused his cock to slide in as deep as it could, making Herman’s mouth widen.

“Ooooh fucking god!” He shuddered. 

Griff moved them to a patch of grass before setting Herman down. He laid back and got all comfortable before letting Herman straddle up for a ride. Rock hard and throbbing, Griff loved feeling that not-so-virgin ass back around his dick.

“Mmm, yeah Herman, ride me! Pound yourself on my dick!” He called out eagerly.

“You’re a dork,” Herman grumbled as he began to awkwardly bounce himself on the five-inch length. His movements weren’t exactly professional level or clean, but it was good enough that both boys were quickly releasing moans once more.

Planting his hands to the boy’s sides, the ex-thief helped guide him up and down. 

They fell into a rhythm of Herman rising off the cock, then Griff using his slim hips to slam back up deep inside. As the younger boy would sit back down onto Griff, he would grind his hips. “Damn, Herman. You really are nearly as good as my ex’s pussy dude.”

“Nearly!?” Herman angrily snapped, flexing his ass tighter with a pout.

“Your ass is fucking sweet man but I still prefer chicks, sorry dude” Griff shrugged, not thinking it was a big deal. “Seriously dude, just wait until you finally get to pound some pus, you will love it.”

Herman rolled his eyes, unable to disagree with him. Instead, he began to slam his ass up and down hard. Even if that five-inch piece of meat was a little painful, the boy took it well and moaned from the sensation of his prostate being milked. If he wasn’t careful, it might just have made him shoot on Griff a second time.

“Ngh, I bet girls would prefer me pounding them more than you!” He exclaimed, vowing to finally sleep with Bailey before their time on the Isle finished.

“With your little dick?” Griff chuckled, definitely noticing the ass trying to milk him. ‘He really doesn’t like being second best,’

Herman pouted but protested back. “You’re not that much bigger! And at least, I still have a girlfriend!”

In retaliation for that comment, the ex-con roughly gripped his new friend’s cock and started to fuck him harder. In cowgirl, it was a little harder, but pounding Herman’s eagerness to show off his body became easy after a few slams. Jerking the boy off with a fast pace, Griff felt all the pre leaking onto his hand. 

Feeling his cock being milked had Herman in a new world of pleasure. He hadn’t thought about jerking off while riding since all he knew of was girls fingering themselves.

“Ngh, h-holy fuck are you trying to get a faceful of cum, Griff?” He laughed, but that led to his defeat. Griff closed his hand tight around the head with a cocky smirk. All Herman could do was ride and whimper as his butt was used as a fuck hole.

“Good point. You’re only worth my hand and your chest,” Griff retorted, smirking at the now growing pout on Herman’s face. The teen used his spare hand to feel Herman up.

Herman continued to pout as he bounced a little harder on Griff’s cock, both boys knowing they were getting a little closer to their release, the younger of the two nearly at it as his body was rocked by both Griff’s cock and his handwork. After releasing a moan, he tried to teasingly convince the other teen. “C-Come on, you would be hot with a face full of my cum.”

“Nope,” Griff hummed, enjoying how tight the boy was, “Cum in my hand and you get my trunks!”

They continued to fuck like rabbits in silence, one grinning and other with a desperate pout. Eventually, however, Herman gave in and allowed his body to release. 

“I h-hate you…” He muttered, feeling every throb as he pumped Griff’s hand full of his sticky hot load.

“Uh-huh, sure you do,” Griff smirked, as he continued thrusting upwards in order to pound on his new friend’s ass, as Herman’s cum fired out into his hand. Filling both his hand and coating the top section of his cock in his own spunk. “Mm, should make you suck this off my hand. You shot a lot.”

Herman muttered, hating himself for enjoying this so much. However, he didn’t want to eat his cum so leaned back and propped himself on both hands. Riding slower, the boy moved up and down the sexy five-inch cock throbbing inside of him.

“Cheeky brat,” Griff rolled his eyes.

“Oi!” Herman growled, the teen recovered enough to pick up the pace bouncing on the cute older boy’s cock. Earning moans escaping from Griff’s mouth as the teen was pulled close to his own orgasm.

Grabbing the boy’s hips to keep him in the air, Griff bucked up from the ground to slam balls deep. His hot load pumping the now-not-so-virgin boy full. “Fuuuuuuuuck yes, milk me!” 

Herman smirked down at the boy as he attempted to tighten his ass around the older boy’s slightly longer cock as he rode the dick with every bit of energy, he had left. Despite wanting to drop down and recover from his second orgasm and numerous close calls in a short period of time. He continued doing this until Griff’s cock finally stopped firing its load inside of him, with Herman feeling every shot as it fired into his ass.

They both collapsed into a sweaty cummy heap, with Herman rolling onto his side so Griff wasn’t able to cuddle him like some guys did in the movies. Griff might be cute but as with the other boy, he wasn’t overly interested in dudes that much. He especially didn’t feel like cuddling with one in his post-sex bliss. He might be willing to have some enjoyable sex with one, but sex wasn’t romance.

He looked back up at the sky and smirked. ‘I’m not a virgin now, Chance! I WIN!’

Unaware that he wasn’t the only Baldwin who had fooled around with Bailey, with the girl having made his older brother swear not to reveal their ill-fated attempt at being more than just friends. However, unlike his little brother, Chance had gone a little further.

“I’ll take those trunks now. I think there’s a crab in mine,” Herman saw the little white crab peek out from his pocket, the poor little thing coated in chocolate.

Griff decided to be a little cheeky first since while he had already decided to help out the other boy, he didn’t want to just give into Herman and let the other boy think he was in control here. “I only said I would consider dude, hmm should I?”

“Well, maybe I will suck you if you say no,” Herman teased, not really considering doing that.

“Oh, so if I say no, then I get sucked? Nice.” Griff teased back, with the teenager not exactly expecting to get blown by the other boy but also not willing to say no to a fairly good looking boy wanting to suck him off. If they wanted to suck his cock, who was he to say no to them.

Now Herman wore a smirk, knowing that his new friend and the boy who had just fucked him was looking forward to getting his cock wet. “I never said when,”

“How about we make a little deal,” Griff grinned, when a cheeky idea came to mind. “We both walk back to the hotel, in our underwear but you owe me something good.”

“Or,” Herman snatched up Griff’s blue-and-pink trunks and slipped inside of them, “You do that, and I owe you double.”

“You owe me double, and I’m fucking your girl.” Griff teased.

“You wish she would be interested in a small cock like you.” Herman teased, as he tied the trunks tighter so they didn’t fall off. “So double owe?”

Fifteen minutes later and there were two teenage boys walking casually down the street chatting as teenagers do. Nothing strange about them to those who weren’t paying any attention. Only weird thing is that they were sticky with cum and sweat, their hair was a mess and one of them only had a pair of tight blue boxer briefs covering him up. The other was in a sensible pair of blue-and-pink trunks that Herman had claimed for keeps, with a pair of black trunks leaking chocolate and dangling a poor hermit crab over his shoulder. Herman eventually noticed it danging there and blinked at the tiny creature with a look of confusion.

As if to say ‘hello’, the hermit crab clamped a tiny claw on his nose.

“Ow…” Herman muttered, tugging it off. “Hey Griff, think we can keep hi-AHH!”

A quiet squeal filled the street as Herman suddenly felt the loose shorts being tugged off, dropping down around his ankles to leave him completely naked. His hard four and a quarter inch cock was semi-hard and now flopped around openly for anyone to see. Not that anyone really batted an eye to the boy. Quickly his hands covered up so nobody could see his cock, not thinking for a moment that he was holding a crab up to his private parts. If it had taken a snip then he would have been screaming for the world to hear.

Griff burst out laughing from the girlish scream. That was the last thing he expected from the younger boy. Just to make things fair, however, Griff stripped as well with no shame whatsoever. He thrust the boxer briefs into Herman’s stiff arms and gave the boy a cheeky smirk.

Wiggling his tight ass at Herman, who felt himself licking his lips and wishing that he had gotten his chance inside of the other boy, Griff started back down the street. “Come on, dude! Who gives a damn if you’re naked, they see that all the time here.”

“I-I still don’t… Ugh!” Herman shuffled along after him. His tan cheeks were a bright pink shade, and he kept looking around to make sure no one was staring. “I hate you,”

Wiggling free, the crab dropped to the sidewalk and scuttled over to the discarded and forgotten black trunks. With one little claw, he gripped on and dragged it back to the beach. A sight that would confuse numerous individuals for years. 

“I guess we aren’t keeping the Hermit…” Griff giggled, keeping a few steps ahead. 

While the teenager was going to torture Herman with his ass; The prankster was covering up a hardened length now rather than a semi that refused to go down despite his embarrassment. Keeping his eyes glued to the ground, struggling not to look at Griff Jones’ fine butt, Herman hoped to god that they were close to the hotel. 

After all, the beach was only a couple minutes away and they had been walking for a while now. So when he looked up to see the tall building a sigh of relief escaped the young boy as he shifted into a brisk pace, eager to get inside and dressed again. Well, as long as Blake wasn’t there. Staying outside nude sounded better than his cousin seeing him in that state. 

Though it could have been worse. Chance could have been around to see him, completely naked. 

His brother had begun to hint at them trying a few things out, which had Herman freaking out from the possibility of Chance thinking that way. He really didn’t want Chance to be possibly jerking off to the thought of him naked, or the possibly of fucking him. Herman definitely didn’t want Chance’s cock to ever get the chance to slide into his ass. Griff’s cock sliding into him was one thing, at least Griff was good looking. Chance had nothing going for him except for being his older brother.

Their little chat on the beach that morning hadn’t done anything to soothe his suspicions, either. In fact all it did was throw their cousin into the mix of strange thoughts and dirty images, with Herman almost positive now that the two older boys wanted to share his body or even take a turn on Bailey, while completely unaware that the older boys actually wanted both. Shivering at the thoughts, Herman sped up to keep track of Griff. He noticed the boy side-eyeing him but stared straight on trying to keep some composure.

It was the individual coming out of the hotel that had Herman’s composure dying quickly, his girlfriend Bailey was about to see more than he had planned.


	3. Chapter 3

“F-Fuck…” Herman whispered internally, as he stopped and attempted to hide his cock.

Walking out of the door to the hotel, Bailey had to giggle as she saw her boyfriend standing there, completely naked. Though the girl admitted to herself that she was loving the view of Herman like that, even if she wished he wasn’t using his hands to cover his cock from everyone’s view.

Even if his extremely cute ass was open to perv on.

“Herman? Uh, why are you naked?”

Herman could only groan in annoyance as the teen reached out and grabbed the towel his girlfriend was holding, and wrapped the pink colored towel around his waist before stalking off into the hotel. Bailey could only giggle as she followed the teenage boy, wondering if she could possibly enjoy more of that view.

A view that definitely looked more fun than the beach.

Muttering, the dark-haired boy looked over his shoulder. “Ask him.”

Turning back, Bailey saw another boy equally naked. Only this one was proudly grinning and rocking a hard dick, not too different in size to Herman. Raising an eyebrow at the pair, Bailey giggled softly. She followed the boys towards the elevator with an avid curiosity, unable to drag her eyes away from either of their cocks. Even if Herman tried his best, it was hard to cover up everything all at once. Bailey didn’t mind one bit.

“And who are you? I’m Bailey, Herman’s girlfriend,” She said with a hint of lust, leaning close to this new boy. “You do know you’re naked in public, right?”

“Oh, I know… I’m giving your boyfriend a view that he won’t forget.” Griff chuckled, before smirking. “Anyway, I’m Griff. Your boyfriend and I went cliff diving.”

Bailey shook her head. Of course Herman had done things with boys, “And you lost your clothes? Not that I'm complaining, but that sounds like bull,”

“We had an incident with a crab.” Griff replied. “And, you know if you’re enjoying the view, your welcome to get a close up…”

“OI!” Herman protested, the towel just managing to hide his naked body.

“Wait until we’re alone, big boy,” Playfully walking closer to Herman, the girl wrapped around his waist for a tight hug. A few small, loving kisses planted on his neck, and Bailey’s hands drawing near to his erection had Herman softly moaning. She loved that sound, as it meant she had the boy wrapped around a little finger to do whatever she feels like. If Bailey felt like it, she would have Blake and Herman on their knees in seconds. “Don’t think you ain’t coming, Hermie. Your new friend sounds like fun,”

Griff chuckled at the attempts of protests coming from Herman being mixed with the boy’s purring from having the girl hugging him. Deciding to torture the boy more, he moved towards Herman and ran a finger down his chest.

“Oh, Hermie knows how much fun I am…”

“Sh-shut up, Griff!” The prankster tried, “The mongoose fi-finds you boring now,”

“Well then, if the mongoose doesn’t want anything, maybe Mrs. Mongoose would like to come and enjoy the cliffs…” Griff purred, as he reached over and lightly rubbed Bailey’s arm.

The naked teen took Bailey’s hand with a giggle coming from the girl, as she played along and allowed Griff to lead her into the hotel. Her boyfriend follows, not wanting Bailey along with his new friend. Stepping between the horny teenagers, Herman pouted and pressed the elevator’s silver button. A short while later they were walking into his hotel room, but he really should have expected what happened the moment they were all behind closed doors. 

The teen turned back from locking the door to find Bailey wrapped tightly around his new friend’s waist, their lips smashing together with a heated passion that made his jaw drop. Griff’s hands were tightly gripping her ass, holding the girl up while kissing her. It was all too obvious that their tongues were going at it as much as they were, and Bailey was moaning around the boy’s lips from the feeling of his cock pressed against her.

All Herman could do was stare and throb, dropping the pink towel to reveal his four and a quarter inch cock once more.

Bailey noticed this just in the corner of her eye, so used one hand to wrap around the length and drag him closer. Her kiss with Griff didn’t break even while she stroked Herman. The girl lost herself slightly from the shock of just how talented Griff’s tongue was, as it fought with hers for domination of her mouth.

After what seemed like forever they broke for air. 

“Damn… that was…” Bailey whispered, blushing at Griff.

The boy gave her a wink and a smirk, which had her blushing and wanting something else from the sexy boy.

With a giggle coming from the girl, Griff was guided in to kiss Herman by the girl. The boys’ eyes widened in shock as they were forced together to share their first gay kiss. Neither could say it was bad, but they definitely would have preferred to make out with Bailey than each other. But her hands were keeping their heads together, so a prideful Griff kissed Herman deeply, pressing his tongue to the prankster’s lips. 

While he wasn’t entirely sure why he did it, Herman felt his lips parting as he allowed Griff’s tongue to slip into his mouth. Despite Griff taking the lead, Herman’s tongue wasn’t going to back down to this and the boy’s tongue engaged in a war for domination that neither boy was willing to lose. The younger of the two, wanting to make sure that his girlfriend stayed interested in him and didn’t get any ideas about Griff.

Griff felt his cock throbbing as Herman fought him, so growled softly into their kiss. This war was going to come out with him on top, even if he had to force the boy into submission again. Pushing his tongue deep as it could go, the boy heard Herman struggle and begin to back down. 

Tugging slightly, Bailey pulled the boys apart and giggled at them. Herman’s lips were still wrapped around the annoying tongue, sucking on the tip just to tease. “I thought you boy’s would be more focused on me, but I can let you two keep making out if you want…”

Griff chuckled internally and winked at his new friend’s girlfriend as he reached out and pulled her closer, bringing the girl into a slightly awkward threeway kiss.

Grinding into his girlfriend’s thigh, Herman rolled his eyes and continued to kiss them both.

“Mmm,” Bailey moaned into them. Two hard cocks was new for her, and all the girl wanted was to play with them. “Think they could both fit in me, guys?”

Herman blushed a deep crimson, imagining her taking the pounding Griff gave to him before. Only now with two dicks in the tiny, tight hole. “A-are you sure, Bailey? You haven’t tried double before and your pussy is tight!”

Griff chuckled, “Didn’t you say, you haven’t tried solo before dude…”

Herman responded with a deeper blush and flipped off the slightly older boy.

“Be nice Hermie… and who said my pussy?” Kissing the sweet boy tenderly, Bailey cupped his soft cheek and smirked. Always so innocent and nice the moment she talked about something new and kinky during sex.

The blush only got worse as he gulped from the implementations of her response. “D-Do you mean your…”

Bailey giggled nervously and blushed a little herself.

“Let’s try me sucking you boys before you get ideas, like that Hermie…” Bailey teased. “If your willing to share me with your sexy new friend…”

Her boyfriend gulped but nodded.

Happily letting her down, the older boy wrapped a hand around his cock while Bailey was grabbing a pair of pillows that she stuffed under her knees. Griff bit his lip as the girl leaned over the bed, getting a nice view of her small but round ass as it wiggled. He nudged Herman, but the dark-haired boy was already staring at it as well. They drooled, but did their best to look natural when Bailey turned back and set up. Once all set up, kneeling by their feet, Bailey took over stroking their sexy cocks. Griff on the left and Herman on the right, jerking the softly moaning boys was fun. She was close enough to smell them and got the faint whiff of chocolate on Herman, amidst the heavy smell of cum. 

She wondered what they had done, but since they had already beaten her to having fun she tightly squeezed. Stroking faster at an unbearable pace to torture the teenagers, Bailey loved the way they suddenly whined and bucked into her palms, unable to keep from trying to fuck the hand. Herman was dripping with pre already, and Griff not too far behind. However, just as they were able to cry out in pleasure and relief, she let them go. 

“Bad boys,” She muttered, letting the cocks twitch and dangle until they softened just enough. The girl was confused about how much cuter both boys looked with softer cocks.

She kept working the two nice and slow, teasing the full length of their cocks. Both of which, she noticed, were cut. Moaning filled the hotel room the more she pleasured the two, growing louder when Bailey planted a small kiss on the throbbing mushroom heads.

“Are you two cuties, ready to have fun?” Bailey asked the pair of mushroom heads, giving them each a second longer kiss. 

A kiss that had the owner of each mushroom head, moaning and ready for their newly formed friendship to move to another level with the addition of Bailey. Both boys found themselves releasing a form of the word ‘Oh yeahhh’. One in a deep moan and the other in a lust leaking growl.

With the girl loving the reactions she is getting from her boyfriend and his sexy new friend.

“Get closer together.” Bailey placed a hand on their hips, forcing the boys to shuffle over closer to one another. This let her place the heads of both cocks together and see the slight difference in size. While Herman was a darker shade of pink, the head of his cock was thin. Griff’s was more girthy and a lighter pink which she found cute. “I’ve always wanted to try two at once… especially ones belong to such sexy boys…”

Leaning down, the girl engulfed their cocks and began to attack the tips with her tongue. Swirling around the sensitive cocks that tasted of cum already, Bailey made sure to get them all slick so she could suck them both.

Quickly a nearly spent Herman was a moaning mess, his tender hands running through Bailey’s curls. He couldn’t help but start moaning loudly as she sunk further down their lengths. “Mmmm oh yeah Bae…”

Griff couldn’t help but snort a little and mutter ‘such a dork’ to the boy he had been inside on the cliffs.

“I-it’s your fault!” Herman hissed in a low voice, bucking into his girlfriend’s mouth. 

Bobbing up and down along the two cocks, Bailey hummed quietly to torture the boys. With their throbbing dicks pressed together and her humming vibrating, the two boys both let out a moan to cut off their argument. With a smirk, Bailey lapped up the taste of their cum and used her tongue to pleasure them like there was no tomorrow. If they got to have their fun, then she could have hers. Which involved hollowing her cheeks a little while taking the two as deep as she could, which was around half. Two cocks weren’t easy to suck, but she was enjoying it. 

Although, a wicked thought crossed her mind.

Reaching her hands around, the young trickster slipped a finger between Herman and Griff’s ass cracks, following down until she pressed against their holes. To her surprise, Herman’s was sticky and dribbled with cum.

“You are such bad boys!” She pulled off with a low growl. Her growl turning into a teasing smirk soon after as she scooped a little of the cum from her boyfriend’s crack and tasted it. “Not bad Griff… fully expected that my boyfriend was a bottom boy.”

“I-I am not!” Herman rebutted, turned on by the sight of her eating another boy’s cum. His cock twitched, betraying his excitement. 

Bailey smirked and forced her finger into Griff’s ass, making the teen boy grunt and squirm around a little from having the girl’s finger exploring his hole. This lasted a few moments before she pulled the finger out and smirked at her boyfriend. “Since there isn’t any in Griff, it means you were his cum dump.”

Using the cum as lube, she worked the other finger into Herman’s cute bubbly butt. Feeling around inside, she felt just how much spunk had been shot into the tight hole. Hoping that Griff had enough left in his to shoot that much into her as well, Bailey pulled out her cum-coated fingers and showed them off. Watching it dribble down her digit, before expertly catching it and sucking the load off. Swallowing Griff’s cum for a second time.

“And such a big load too.” She teased.

Griff smirked at the younger boy, slinging an arm around his shoulder. Pulling Herman close, the jailbird proudly described some of their sex. Even with a few words, it was enough to make Herman blush/ “Oh, that’s nothing on the first one I shot! It was so big it hit Herman in the face! I was jerking our cocks together and we shot all over Herman. You should have seen him covered in it...”

Of course he left out their kiss, remembering the sweetless of Herman’s mouth as he had shared their combined load of cum. That was something just for them to know. Which based on Herman’s blush, was something that Herman was remembering.

“Maybe you can show me how you did that tomorrow? Or later tonight, if you two aren’t empty when I’m done with you.” Sucking on Griff’s cock, Bailey showed her skills by deepthroating the boy’s thickish cock. 

“M-May-maybe…” Herman blushed, his cock throbbing as he watched his girlfriend sucking his new friend’s cock. Some part wished of Herman that it was him down there blowing Griff, getting to taste that yummy cock for the first time. But, still convinced he was a straight boy, he watched instead and stroked his four and quarter inch cock. Slowly so that he wasn’t getting too close to the edge already. “You sh-should suck on mine, too.”

Bailey pretended not to hear him, instead worshiping Griff’s five-inch cock. With one hand around the base jerking him off, she sucked on the throbbing head at a fast pace. Adding tongue to made the jailbird groan loudly, fucking into her mouth as the feeling became more intense. Bailey’s dark eyes moved slowly up the young hunk’s body, before finally they locked eyes. Slowly, she trailed her tongue along the underside of his cock while pulling off. Only to slap the cock against her cheek, smearing around saliva and precum.

“Mm, like my throat Griff? Your friend’s girlfriend blew you after you fucked his cute butt…” The words dripped with lust.

“Ohhh yeah… though so far Herman here has you beaten for best blowie...” Griff smirked, teasing his new friend. With Herman’s blush getting worse when Griff reached over and gave his ass a very gentle spank.

“I-I-I didn’t!” Herman blushed heavily, at the thought of his girlfriend thinking that he sucked Griff’s sexy cock. “Really! I didn’t s-suck him! He just knows…”

Bailey and Griff rolled their eyes playfully, with the two quick to wrap a hand around his slightly smaller cock. While surprised by each other, the pair started to pump along Herman’s cock nice and slow. The two hands were able to make Herman whine loudly and his body to tense up. A dribble of precum poured from the boy and down their fingers, but Griff and Bailey didn’t bother to stop. Still bobbing up and down while she jerked her boyfriend, Bailey felt a hand on the back of her head. It moved her faster up and down along the length, with the girl struggling slightly when Griff’s cock hit the back of her throat.

“G-Griff… B-B-Bailey…” Herman moaned out, with Bailey frowning internally as she realised that her boyfriend had moaned the other boy's name first.

“Would you like something, Herman?” She asked, after pausing her movements on Herman’s cock as punishment and taking a long lick up the length of Griff’s cock.

Herman opened his mouth but was only able to release a loud whine as he watched his girlfriend’s tongue working the length of his new friend’s cock. With the boy pulling back into a pout. “H-Hey! Why did you stop!”

“Because you are getting down here to help!”

Flashing a cheeky smile, the pretty girl took Herman’s hand and dragged him down onto his knees beside her. She planted a firm kiss on his lips, sharing a little of Griff’s precum with her tongue before breaking off. Oh how she loved the way Herman blushed, and how his pink lips shook in shock even though he had done worse without her. Once Griff had stepped closer to the couple, he put his cock between their lips and chuckled when Herman very quickly gave the head a long lick. He just couldn’t help it, really. The boy needed a taste at least. Though that wasn’t to say he stopped at one lick. Soon joined by Bailey, who followed down the length rather than the head.

“B-Bu-But… I-I don’t want to suck a cock…” Herman attempted, blushing as he recalled the numerous times in the past where he had been forced to use his mouth to relieve some individuals. Most commonly his older brother Chance and cousin Blake.

Based on the reaction of his family and the other guys, he had sucked. He did have talent, but he wasn’t sure he was ready to suck Griff yet since he didn’t want his new friend to see him as a bottom.

“Oh, okay then babe. Griff would you like to be my new boyfriend?” Casting a cocky smirk at her ‘ex’, Bailey kissed along Griff’s balls.

Herman growled but decided to call her bluff.

“Fine! Date him!” Herman glared, as he got up and began to storm out of the room. Internally smirking as he waited for Bailey to beg for his return.

However, it was Griff’s voice that cut in first. A slyness to his words, dripping with lust just to annoy the hell out of Herman. Sure enough, it worked and Herman was livid.“Sure thing, babe. I’ll take you on a little moon-lit walk down the beach tonight. Pick you up at eight?”

“Cum at seven and I’ll make sure you're all nice and relaxed for our little date…” Bailey purred back, making sure her boyfriend heard every word.

Without a single word, the younger boy walked back into the hotel room. He wore an angry expression even when abruptly kneeling down and grabbing hold of his new friend’s dick. A little too hard, as it made Griff wince. 

“She is mine…” He muttered as he leaned in and engulfed his new friend’s cock. Blushing as he realised that he was now sucking on the cock that not that long ago was pounding his young ass.

However, that sound turned into a moan as he felt the angry boy’s throat wrapping around his cock, able to take the whole thing inside with one swift movement. Herman bobbed along the cock at a fast pace, taking it deeper so he buried in Griff’s small bush. Feeling it as the boy’s cock throbbed inside, dripping pre onto his tongue. Mouthing something, Bailey watched in awe as her real boyfriend sucked dick like a pro. Deepthroating the five inch cock like it was nothing and barely stopping for air. Something Herman usually was terrible at, but some other force was driving him this time. 

“W-Woah… Hermie…” She whispered, wondering if her boyfriend had sucked before.

Bailey found herself eager to join back in, so leaned underneath the boys and took one of Griff’s nuts into her mouth. 

Griff couldn’t manage any words, too lost in the overwhelming skills the two were providing his cock. If they kept up any longer he would be completely spent for the day, having shot two loads earlier. So, though it took all of his might, the jailbird pulled the mongoose off his cock and reeled back. He tripped on the bed, falling back onto it.

“O-okay you can stop… da-damn… You didn’t tell me you were a pro cocksucker!” He exclaimed, amazed that his cock was still throbbing so heavily even once Herman was off his cock.

Herman smirked. “Your turn to return the favor. If you want me to let you get away with trying to date my girl…”

Blushing a bright red, the older boy scrambled up the bed. Taken aback by the sudden shift in Herman’s personality from a meek cute boy to a suddenly dominant top, Griff gulped. His eyes followed down the tan boy’s naked body to his four and a quarter inch cock, watching it twitch while Herman climbed up onto the bed. Though he didn’t stop there, opting to straddle Griff’s chest and sit on the boy to pin him down.

“Bu-but I haven’t, um… su-sucked anything for a long time…” He admitted, remembering the times in juvie his mouth became a toy. Around the house that wasn’t the case as much, with his mouth being cock free for about three months so far. “Ngh, do I have to?”

“I sucked yours…. So it’s only fair, Griff…” Herman purred, with the boy reaching under to run his finger over Griff’s ass. Letting his new friend know that he would be expecting a chance to top him as well. But that was for later, as the mongoose started to slap his dick against Griff’s lips. “Open wide for me?”

Bailey sat on the edge of the bed, watching them for now. The girl wondered if she should be a little jealous of the new boy in her boyfriend’s sexual life, a question that only grew as she watched Griff’s mouth opening and Herman’s cock sliding deep inside.

Griff was hesitant to start moving, but grew calmer on the cock gently fucking his mouth. Working his throat around Herman’s cute length, the ex-con got back into his old rhythm pretty fast. Up with the tongue, and down to deny them. It seemed to be working on the other boy, since Herman was quickly biting his lip. The young teen wondered what felt so different this time, with Herman’s cock feeling almost comfortable as he sucked on it, in comparison to the disgust he felt previously. 

“O-oh fuck…!”

Unable to just sit there wondering about the future of their relationship, Bailey moved over to the pair and set herself up in Griff’s lap. Since he was nicely lubed up with spit, the girl had no worries when she lined him up with the tighter of her two holes. Sitting on the head, she felt Griff begin to enter her ass slowly, stretching her open like Herman couldn’t. Even from around a cock they could all hear the jailbird’s cry of passion feeling the two working his body. Herman was deep down his throat, and Bailey was sinking her ass down on his cock.

She might be doubting her relationship but her pussy was for Herman.

“A-agreed!” She moaned, as she eased down the entire length of Griff’s cock.

Herman looked back, releasing a moan. His own girlfriend was sitting on another boy’s cock, who happened to be sucking on his dick at the same time. This was the last thing expected to happen on vacation, but something the boy instantly fell in love with. What made it better was that the other boy wasn’t Chance. Instead, it was someone who was actually pretty good looking even for someone who at best would consider himself bi-curious.

Griff was in heaven taking it from both ends, a tight hole riding his cock like a skimpy pro while a boy fucked his mouth. Able to fully taste every inch of Herman’s cock, his tongue wrapping around the thin length and loving his musky boyish flavour. He could taste the cum on Herman’s cock trickling down his throat, and the odd sweetness of chocolate from his pockets. Something that made the jailbird roll his eyes playfully. 

As the boys moaned for each other, Bailey snapped her hips up and down taking Griff balls deep in her ass. Feeling it throb against the walls every time she went down on the boy’s dick. 

“Mmm, fuck me Griff! Don’t you two ignore me!” Bailey demanded as a pair of hands lightly touched her hips. Beneath her Griff shifted around to prop up his legs before using his hips to slam harder into the girl. She cried out in pleasure, “YES!”

Herman wrapped both arms around the back of Griff’s head as he pounded the boy’s mouth, his small moans husky. “Aw fuck yeah… fuck my girl, dude! She’s so tight,”

Grunting slightly as he fucked Herman’s girlfriend harder, Griff pulled off then managed out. “If you think she’s fucking tight man, you should try my girl… Zuri’s pus literally milks your cum out of you…”

The couple snorted at Griff as they continued to work him; Both of them knew that Bailey was tight enough on her other end that Herman never stood a chance to get away without cumming inside of her pussy. So to show this off he pulled out and slapped Griff across the face with his dick.

”Don’t be an ass, Griff… we both know Bailey’s way better…” Herman grinned.

“Just wait dude, just wait…” Griff smirked, earning him a second dick slap from the other boy and a giggle from said boy's girlfriend.

After climbing down to join the hot pair and pressing the tip to Bailey’s dripping wet pussy even as Griff busied himself ramming in and out of her tightness. Herman leaned in and planted a soft kiss on her lips, swallowing the loud moans of delight pouring from her. Only for those sounds to grow louder as he too slid his cock inside Bailey, giving her the first ever double penetration.

Bailey couldn’t manage words as two cocks eased their way into her, with the boys able to feel the other shaft through her walls. They all moaned as one filling her up, not sure how long they would be able to last in what were easily the tightest holes they had ever been inside of. The only rival being Herman’s own not-so-virgin ass now.


End file.
